Senior Director, Customer Success

Grammarly is excited to offer a remote-first hybrid working model. Team members work primarily remotely in the United States, Canada, Ukraine, Germany, or Poland. Certain roles have specific location requirements to facilitate collaboration at a particular Grammarly hub.

All roles have an in-person component: Conditions permitting, teams meet 2–4 weeks every quarter at one of Grammarly’s hubs in San Francisco, Kyiv, New York, Vancouver, and Berlin, or in a workspace in Kraków. This flexible approach gives team members the best of both worlds: plenty of focus time along with in-person collaboration that fosters trust and unlocks creativity.

Grammarly team members in this role must be based on the West Coast of the United States or Canada, and they must be able to collaborate in person 2 weeks per quarter, traveling if necessary to the hub(s) where the team is based.

The opportunity

Every day, tens of millions of people and 50,000 professional teams worldwide trust Grammarly’s AI and human expertise to help ideate, compose, revise, and comprehend communications. Our team members have the autonomy to take on exciting challenges in pursuit of our mission to improve lives by improving communication. Together, we’re building on more than a decade of steady growth and profitability. We’re defining the communication assistance category with our tailored service offerings: Grammarly Free, Grammarly Premium, Grammarly Business, and Grammarly for Education. Our latest product offering, GrammarlyGO, brings the power of generative AI to our users. It all begins with our team collaborating in an inclusive, values-driven, and learning-oriented environment.

To achieve our ambitious goals, we’re looking for a Senior Director of Customer Success to join our Sales Leadership team. This person will drive positive business outcomes for our customers through value realization initiatives that lead to expansion and learnings. They will report directly to the Head of Customer Success for Grammarly’s B2B business and will lead a team of front-line managers. As our first Senior Director of Customer Success, they will be responsible for developing and executing strategic initiatives, and owning revenue-related targets including pipeline generation, expansion, and Net Dollar Retention. The Senior Director of Customer Success will collaborate cross-functionally with teams such as Sales, Product Management, Revenue Operations, and Product Marketing, and the broader growing the team to support our ambitious growth goals for 2023 and beyond.

Your impact

As the Senior Director of Customer Success, your team and work will have high visibility. You will be a driving force of revenue growth, high customer satisfaction, and actionable insights, and you will be a strong advocate for both the customer and for your team. Your leadership team will be responsible for scaling a top-performing Sales ecosystem.

You will be evaluated and compensated based on the Customer Success team’s performance, initiatives to grow the customer success function, and role-modeling Grammarly’s EAGER values (ethical, adaptable, gritty, empathetic, and remarkable).

  • Your first 30 days will be focused on learning. You will gain a deep understanding of our customers, our product, our value proposition, aspects of sales performance, the sales tech stack, and our value-based sales framework.
  • By the end of month three, you will have recruited new team members, created and tested new playbooks, evaluated performance measurement, and developed a clear, strategic plan for the year ahead. Your team will be consistently meeting pipeline generation, quota and NDR expectations.
  • By the end of month six, you will have developed a highly effective operating cadence, captured performance improvements, and established a predictable and repeatable enterprise customer success motion.
  • By the end of year one, you will have built out a best-in-class Customer Success function that is ready to efficiently and effectively support a fast-growing and global customer base.

We’re Looking For Someone Who

  • Embodies our EAGER values—is ethical, adaptable, gritty, empathetic, and remarkable.
  • Lives on the West coast of the United States or Canada and is able to collaborate in person 2 weeks per quarter, travelling if necessary to the hub where the team is based.
  • Relentlessly sets aggressive short and long-term goals and possesses a strong internal drive to achieve them.
  • Builds and deepens relationships with people, understands their needs and goals, and sees solutions through.
  • Searches for reasons and causes and has the ability to synthesize quantitative and qualitative data, make data-driven decisions, and use (often incomplete) data to identify gaps and opportunities.
  • Wants to bring stories to life, energize them, and make them exciting and vivid—in other words, takes dry ideas and enlivens them with images, examples, and metaphors.
  • Discovers how to realize business value and expand customer relationships through a deep understanding of customer needs, rather than a feature list.
  • Understands the subscription business models including Freemium, free trial, account expansion, and upsells.

Support for you, professionally and personally

  • Professional growth: We believe that autonomy and trust are key to empowering our team members to do their best, most innovative work in a way that aligns with their interests, talents, and well-being. We support professional development and advancement with training, coaching, and regular feedback.
  • A connected team: Grammarly builds a product that helps people connect, and we apply this mindset to our own team. Our remote-first hybrid model enables a highly collaborative culture supported by our EAGER (ethical, adaptable, gritty, empathetic, and remarkable) values. We work to foster belonging among team members in a variety of ways. This includes our employee resource groups, Grammarly Circles, which promote connection among those with shared identities, such as BIPOC and LGBTQIA+ team members, women, and parents. We also celebrate our colleagues and accomplishments with global, local, and team-specific programs.

Compensation And Benefits

Grammarly offers all team members competitive pay along with a benefits package encompassing the following and more:

  • Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)
  • Disability and life insurance options
  • 401(k) and RRSP matching
  • Paid parental leave
  • Twenty days of paid time off per year, eleven days of paid holidays per year, and unlimited sick days
  • Home office stipends
  • Caregiver and pet care stipends
  • Wellness stipends
  • Admission discounts
  • Learning and development opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US and Canada locations are categorized into compensation zones based on each geographic region’s cost of labor index. For more information about our compensation zones and locations where we currently support employment, please refer to this page. If a location of interest is not listed, please speak with a recruiter for additional information.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected “On Target Earnings” (OTE) for this role by compensation zone are outlined below and may be modified in the future.

United States

Zone 1: $280,000 – $360,000/year (USD)

Zone 2: $252,000 – $324,000/year (USD)

Zone 3: $238,000 – $306,000/year (USD)

The commission portion for this role will be 20% of the On-Target Earning (OTE).

We encourage you to apply

At Grammarly, we value our differences, and we encourage all—especially those whose identities are traditionally underrepresented in tech organizations—to apply. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Grammarly is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada).

Please note that EEOC is optional and specific to US-based candidates.


All team members meeting in person for official Grammarly business or working from a hub location are strongly encouraged to be vaccinated against COVID-19.






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